Powerful people often become conservative. Once they’re in charge, it’s easy to feel that all the beliefs that helped them rise into power are all they need to continue to succeed. This means that despite the easy rhetoric about wanting progress and new ideas, many bosses are hard to convince to try new things (such as working remotely or changing culture). They have more to lose now, so their preference for the status quo increases.
Many of us read books, take courses and go to events, often with the support of our bosses, hoping to learn new ideas to incorporate back into the team. But often this is just a pretense, a way to pretend like new ideas are being explored. It often takes dedicated effort to get the support needed to bring a new idea or way of working into practice.
Here’s a quick guide for how to convince your boss:
- Have a great reputation. The best leverage you have with any boss is your performance. They are far more likely to consider suggestions from the highest performing person on the team than the lowest. Before you launch into tirades about the grand revolutions you want them to lead, make sure you’re in good standing. Be patient. Match the size of your suggestion to the quality of your reputation.
- Consider what problems your boss needs to solve. Don’t start with your problems or what things you want to try. Instead think about the world from the perspective of your boss. What are their goals? What do they need to do to succeed? What achievements are they striving for? What will get them promoted?
- Match what you want to try to their goals. Frame anything you want to try in terms of how it might help your boss. Will it have a chance of helping reach their sales quota? Will it help them get better clients? Will it save them budget? At minimum, think about your own productivity and morale: why should your boss care about improving these things? Consider that and make it part of your pitch. You may discover that there are far better things to suggest than the idea you originally had.
- Get support from respected coworkers. If your idea is interesting and possibly beneficial, it shouldn’t be hard to get a coworker or two to also want to try the new thing. Provided the boss respects their opinion, their interest in participating helps support your arguments. In some cases it might even be better if someone other than you makes the pitch. If you have a good relationship with the peers of your boss, especially peers they respect, consider trying to get them involved.
- Look for books and respected organizations that support the thing you want to try. Find companies your boss respects that already use the practice you have in mind. There are often books and papers that can help support your case. Of course getting your boss to read them is another matter, but your consumption of them will better inform you of answers to questions your boss is likely to have, and most importantly, refine your own thinking about the realities of the thing you want to try. Maybe it’s not such a good idea. Or perhaps there is a different way of thinking about the problem that’s more useful.
- Plan for a trial. Minimize their sense of risk by suggesting you try the new thing on a trial basis: a week or a month. Also propose a list of criteria for how to evaluate if the new thing was successful after the trial is over. If you’ve never pitched your boss on anything before, pick the smallest simplest version of the thing you want to try to minimize the risks and earn some trust for the next time you have something you want them to try. Pick a safe and small project that has the fewest risks, or that is only of moderate importance.
- Make the pitch. Remember that most people in power respond differently to pitches when they are in front of a group vs. when they are by themselves. Find a situation that provides the best opportunity, based on when your boss is most responsive to suggestions (email? in your performance discussions? at coffee?) Define the problem (in terms the boss relates to), offer the solution, define the (trial) terms, and reference what other companies already participate. Observe how other people pitch your boss and what tactics work best (See: How To Pitch An Idea).
- Work very hard to make the trial work. Your future reputation is on the line in the trial. If the trial goes well, and they agree to the change, you’ll be in higher standing for the next recommendation you make and convincing them again will be far easier. If you fail, and fail badly, it will be harder to earn their trust next time. Do everything in your power to make sure that failing all else some useful lessons are learned, enabling the argument that doing trials, even if they fail, have minimal risk and provide new lessons for the organization. Including the discovery of new trials to do that might have better results.
In the end, it shouldn’t be all that hard to convince a smart, wise, progressive boss to try new things on a trial basis. If you realize that your boss is impossible to convince, the thing you might need to try is looking for a new boss to work for.